HCID 54490045, compound → Triphenylcarbinol

HRID 1974845Notes

Reaction equation

C(OCC(C[O:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)CCOC(=O)C)(=O)C>C(O)(=O)C>[C:15]([OH:14])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Trityloxymethyl-1,4-butanediol diacetate (60.90 g, 0.136 mol) was dissolved in acetic acid (320 ml) at 100° C. for 15 min, evaporated in vacuum to small volume and cooled to 0° C. The precipitate was filtered off and washed with cold ethyl acetate to give 26.44 g (theory 35.51 g) of tritylalcohol. The combined filtrate was evaporated to small volume. The compound was purified on a silica gel column (500 g SiO2); eluent 0-2700 ml ethyl acetate+n-hexane (1+1), 2700-3740 ml ethyl acetate+n-hexane (2+1), then neat ethyl acetate. The fractions 2540-4800 ml were evaporated to give 14.20 g (51%) of pure 4-acetoxy-2-hydroxy-methylbutyl acetate. TLC on silica (ethyl acetate+n-hexane 1+1): Rf 0.30.

Workup

customevaporated in vacuum to small volume
filtrationThe precipitate was filtered off
washwashed with cold ethyl acetate

Sources & evidence

ORD record: ord-04cdd647b12045a8871ca7d4d82c4423
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05284837

Reaction notes

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