3base (Newbee)
06-04-02 07:00
No 317495
      THF > ClBuOH > ClBuOOH > GHB  Bookmark   

tetrahydrofuran --> 4-chloro-butan-1-ol

4-chloro-butan-1-ol --> 4-chlorobutanoic acid

4-chlorobutanoic acid --> GHB
 
 
 
 
    3base
(Newbee)
06-04-02 07:02
No 317497
      THF --> 4-chloro-butan-1-ol
(Rated as: excellent)
 Bookmark   

THF + HCl(g) ,yield 96%
THF + HCl(aq),yield 34%
(delta-chlorobutanol = 4-chlorobutanol)
Patent US2868850 (Patent GB788349, Patent DE1040523)

tetrahydrofuran --> 4-chloro-butan-1-ol
aqueous hydrochloric acid, tetrachlorosilane
additional  product: silicic acid tetrakis-(4-chloro-butyl ester)
chem listy, 1958 52, 151; kratochvil, frejka
chem abstr, 1958, 16329

tetrahydrofuran --> 4-chloro-butan-1-ol
hydrochloric acid
j amer chem soc, 1934 56, 1596; starr, hixon

tetrahydrofuran --> 4-chloro-butan-1-ol
hydrochloric acid, temperature 40C
justus liebigs ann chem, 1955 596, 65; reppe et al

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl, yield 55%
liebigs ann chem, 1991 8, 783-788; (english); kenji mori, jiang wu

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl, bei siedetemperatur
book review / secondary ref: org synth coll vol II <1943>571; starr, hixon
j amer chem soc, 1934 56, 1596; starr, hixon

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl(g), yield 57%, heating
j org chem ussr, 1987 23, 112-115, (engl transl); a kh khusid
zh org khim, 1987 23 1, 126-129; (russian); a kh khusid

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl gas, temperature 0C
j chem soc perkin trans 1, 1993 17, 2047-2054; (english)
leslie crombie, david haigh, raymond c f jones, ab rasid mat-zin, Ab. Rasid

tetrahydrofuran --> 4-chloro-butan-1-ol
BH2Cl*SMe2
tetrahedron, 1998 54 31, 8919-8932; (english)
Martinez-Bernhardt, Rolando; Castro, Peter P.; Godjoian, Gayane; Gutierrez, Carlos G.

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl, Solvent H2O, temperature 100C
j org chem, 1998 63 1, 152-162; (english)
Pearson, Anthony J.; Gontcharov, Alexander V.
Edit: Retrieved and posted in Post 454558 (Rhodium: "Prep of 4-Chlorobutanol from THF/HCl(aq)", Tryptamine Chemistry)

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl(gas), heating , 6h, yield 45g
chem phys lett, 1999 300 3-4, 493 - 498; (english)
Mohan, Hari; Maity, D. K.; Chattopadhyay, S.; Mittal, J. P.

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl, temperature < 40C
justus liebigs ann chem, 1955 596, 65; reppe et al

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl
collect czech chem commun, 1973 38, 1528-1536; (english); j pola et al
bull soc chim fr, 1971, 4341-4350; (french); e brown et al

tetrahydrofuran --> 4-chloro-butan-1-ol
aq HCl
j gen vhem ussr, 1966 36, 1629-1632; (engl transl); d n andreev, g s afanas'eva
zh obshch khim, 1966 36, 1628-1633; (russian); d n andreev, g s afanas'eva

tetrahydrofuran --> 4-chloro-butan-1-ol
(1) AcCl, ZnCl2
(2) MeOH, HCl
multistep reaction
bull soc chim fr, 1964, 967-972; (french); j huet

tetrahydrofuran --> 4-chloro-butan-1-ol
HCl gas, heating, 5h, yield 82%
j org chem ussr, 1980 16 10, 1728-1733; (engl transl)
Kovalev, B. G.; Matveeva, E. D.; Stan, V. V.; Vovk, G. A.; Yudin, L. G.; Kost, A. N.
zh org khim, 1980 16 10, 2032-2038; (russian)
Kovalev, B. G.; Matveeva, E. D.; Stan, V. V.; Vovk, G. A.; Yudin, L. G.; Kost, A. N.

tetrahydrofuran --> 4-chloro-butan-1-ol
hydrochloric acid, heating, 8h, yield 45%
j org chem, 1981 46 16, 3361-3364
Barry, Carey N.; Evans, Slayton A.
Edit: Retrieved and posted in Post 454558 (Rhodium: "Prep of 4-Chlorobutanol from THF/HCl(aq)", Tryptamine Chemistry)

Reaction Details 14 of 14
tetrahydrofuran --> 4-chloro-butan-1-ol
HCl-gas, 50C, yield 21%
Bouchard, H.; Renard, P. Y.; Lallemand, J. Y.
tetrahedron lett, 1991 32 42, 5953-5956, (english)
 
 
 
 
    3base
(Newbee)
06-04-02 07:04
No 317498
      4-chlorobutanol --> 4-chlorobutanoic acid  Bookmark   

4-chloro-butan-1-ol --> 4-chloro-butyric acid
aqueous nitric acid
j chem soc, 1952, 4492 4495; crawford, plant

4-chloro-butan-1-ol --> 4-chloro-butyric acid
aqueous sulfuric acid, chromium (VI)-oxide
j amer chem soc, 1956 78, 2255 2256; pattison et al
j org chem, 1956 21, 883 885; pattison et al

4-chloro-butan-1-ol --> 4-chloro-butyric acid
indian j chem sect b, 1981 <B> 20 4, 340-342; (english)
k k mathew, p s raman, t g antharjanam bhargavi

not exactly this rnx, but looks also quite well:
butanol + HNO3 --> butanoic acid
Patent GB771583
 
 
 
 
    3base
(Newbee)
06-04-02 07:05
No 317500
      4-chlorobutanoic acid --> GHB  Bookmark   

4-chloro-butyric acid --> 4-hydroxy-butyric acid / butyrolactone
temperature 180-200C
die saeure bezw.ihr lacton, das butyrolacton entsteht
bull soc chim fr, 1886 <2>45, 341; henry
chem zentralbl, 1898 69 II, 273, (german); henry